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Topic: The function of Cu/Benzene  (Read 3241 times)

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Offline SVXX

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The function of Cu/Benzene
« on: June 15, 2010, 06:56:41 AM »
Hello all...this is my first post in these forums and surely won't be the last!

My query is regarding the mechanism/way of functioning of the reagent Cu in Benzene.
I have a substrate, namely diphenyl dichloro methane. When I react it with the reagent in question, I get the product (Ph)2C=C(Ph)2.
I have no idea how this occurs. At first I thought of an alpha-elimination catalyzed by copper to form a carbenoid...but I don't seem to understand how it will result in an alkene.
So I'd be grateful if someone could pinpoint the mechanism of the reaction to me.
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Offline g-bones

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Re: The function of Cu/Benzene
« Reply #1 on: June 15, 2010, 02:20:44 PM »
carbenoids dimerize to form alkenes.  Think about as if its a singlet carbene (even though it is likely a triplet carbene).  The pair of electrons in the filled orbital of one carbene (A) will enter the empty orbital of another carbene (B).  at the same time the electrons in the filled orbital of B  can enter the empty orbital of carbene A.  overall a double bond is formed.

Offline SVXX

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Re: The function of Cu/Benzene
« Reply #2 on: June 15, 2010, 03:42:47 PM »
Ah many thanks...I looked up carbene dimerization and found http://wikipedia.org/wiki/Persistent_carbene as a result. One such example is in diamino-carbenes : http://en.wikipedia.org/wiki/File:Diaminocarbene_dimer.png. Diphenylcarbene is also a persistent carbene it seems, as it is stable.
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Offline AnkurGel

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Re: The function of Cu/Benzene
« Reply #3 on: June 16, 2010, 09:03:34 AM »
@SVXX: That solved the Trouble of The Day
It's a strange thing, but when you are dreading something, and would give anything to slow down time, it has a disobliging habit of speeding up.

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